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$221+ Cheap flights from Aspen (ASE) to Midway (MDW)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
ASE — MDW
Jan 25 — Feb 11
Sun 1/25
Sun 2/1
1 adult, Economy
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Cheap flight deals from Aspen to Midway

Cheapest flights from Aspen to Midway
Explore the most affordable flight options available from Aspen to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 26, 2025.

This Delta deal was found by Cheapflights users on 12/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:20 pmASE - MDW
1 stop8h 02mDelta
Mon 1/56:45 amMDW - ASE
1 stop8h 31mDelta
Deal found 12/25$930

Find flight deals from Aspen to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Aspen (ASE) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 26, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$370
(Delta)

One-way from

$221
(Delta)

Popular in

May

Cheapest in

April

Average price

$530
Provider with most accurate pricing for Aspen Pitkin County-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Aspen Pitkin County-Chicago (CHI) flights.
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From Aspen Pitkin County to Chicago Midway
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One-way flight from Aspen Pitkin County to Chicago Midway
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($15 potential savings vs. average RT price).
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Average for round-trip flights in December 2025
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Cheapflights Fare Finder

 
Customize your flight search to find flights from Aspen to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 26, 2025.
Use the filters below to find and compare flights from Aspen to Chicago Midway Airport that are best for you.

Fly from

Aspen

Fly to

Midway

Route

Depart

Return

Price

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 1/31

3:04 pm-10:22 pm

1 stop6h 18m

Chicago Midway

Mon 2/2

6:00 am-11:43 am

1 stop6h 43m

$370

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sat 1/17

3:04 pm-10:07 pm

1 stop6h 03m

Chicago Midway

Mon 1/19

6:00 am-2:16 pm

1 stop9h 16m

$370

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 1/9

3:04 pm-10:07 pm

1 stop6h 03m

Chicago Midway

Tue 1/13

6:45 am-2:16 pm

1 stop8h 31m

$451

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 1/9

3:04 pm-10:07 pm

1 stop6h 03m

Chicago Midway

Mon 1/12

6:45 am-2:16 pm

1 stop8h 31m

$505

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Fri 1/16

3:04 pm-10:07 pm

1 stop6h 03m

Chicago Midway

Sun 1/18

6:45 am-2:16 pm

1 stop8h 31m

$586

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Tue 3/3

1:36 pm-10:33 pm

1 stop7h 57m

$221

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Thu 1/15

3:04 pm-10:07 pm

1 stop6h 03m

$280

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Sun 4/5

3:00 pm-10:31 pm

1 stop6h 31m

$590

AspenChicago

ASE - MDW

ASEMDW

Aspen Pitkin County

Mon 4/6

3:00 pm-10:31 pm

1 stop6h 31m

$620

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/25

Best time to book a flight from Aspen to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Aspen with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Related info for your journey

Find useful and relevant information for your journey from Aspen to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Aspen to Chicago Midway?

    Located just 3.5 mi from the city center, Aspen Pitkin County is the airport most travelers will use when flying to Chicago Midway from Aspen. Booking flights from Pitkin County (ASE) to Chicago Midway should be relatively easy as there are 0 daily outbound flights to Chicago Midway from 0 different airlines.

  • How long is the flight from Aspen to Chicago Midway Airport?

    Departing from Aspen to Chicago Midway Airport will take you 6h 18m. The distance between Aspen and Chicago Midway Airport is about 1017 mi.

  • Can I find deals for flights from Aspen to Midway that include hotel bookings?

    Yes. In addition to deals on Aspen to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Aspen to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Aspen to Midway.

  • Can I find deals for business class flights from Aspen to Midway?

    Yes. Cheapflights offers flight deals from Aspen to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Traveling to a place near Chicago Midway Airport?

Book flights to Chicago Midway Airport if you plan to visit one of these locations
Lansing
Merrillville
Hammond
Porter
Benton Harbor

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